1H-1,2,4-Triazole → 4-Fluoro-3-(fluoromethyl)-3-methyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one

HRID 1732168Notes

Reaction equation

HRID 1732168 reaction equation
[F:1][CH2:2][C:3]([CH2:9][F:10])([CH3:8])[C:4](=[O:7])[CH2:5]Br.[NH:11]1[CH:15]=[N:14][CH:13]=[N:12]1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[F:1][CH2:2][C:3]([CH2:9][F:10])([CH3:8])[C:4](=[O:7])[CH2:5][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 130194343,3-Bisfluoromethyl-1-bromo-butan-2-one

Product 1

HCID 135325004-Fluoro-3-(fluoromethyl)-3-methyl-1-(1H-1,2,4-triazol-1-yl)butan-2-oneYield 36.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

215 g (1 mole) of crude 3,3-bisfluoromethyl-1-bromo-butan-2-one were added dropwise to 84 g (1.2 moles) of 1,2,4-triazole and 165 g (1.2 moles) of ground potassium carbonate in 1 liter of ethanol at 30° to 35° C. The mixture was subsequently stirred at 40° C. overnight, the insoluble material was then filtered off and the filtrate was concentrated. The oily residue was extracted with methylene chloride and water and the extract was dried over sodium sulphate and concentrated. The residue was taken up in methylene chloride and 140 ml of ethereal hydrochloric acid were added. The crystalline product formed was filtered off with suction and extracted by stirring with 1 liter of methylene chloride and 1 liter of saturated aqueous sodium bicarbonate solution, and the extract was washed with 1 liter of water, dried over sodium sulphate and concentrated. 73.8 g (36.4% of theory) of 3,3-bisfluoromethyl-1-(1,2,4-triazol-1-yl)-butan-2-one were obtained as an oil, which could be further reacted directly. ##STR35##

Workup

  1. filtrationthe insoluble material was then filtered off
  2. concentrationthe filtrate was concentrated
  3. extractionThe oily residue was extracted with methylene chloride and water
  4. dry with materialthe extract was dried over sodium sulphate
  5. concentrationconcentrated
  6. addition140 ml of ethereal hydrochloric acid were added
  7. customThe crystalline product formed
  8. filtrationwas filtered off with suction
  9. extractionextracted
  10. stirringby stirring with 1 liter of methylene chloride and 1 liter of saturated aqueous sodium bicarbonate solution
  11. washthe extract was washed with 1 liter of water
  12. dry with materialdried over sodium sulphate
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-95bf875802db403c8dd4e6b043b6d2e1
Source dataset
uspto-grants-1986_11
Patent number
US04625066

Reaction notes

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